WEBVTT

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Man in the middle attacks are a big issue in today's I.T. Security world.

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So that's what we're going to be doing in this episode Now first of all let's make sure we know what

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a man in the middle attack is on the Internet on any TCAP IP network.

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You have some type of communication going on between two computers.

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You might have a web browser or access to a web page or an S-sh client accessing an S-sh server or a

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computer accessing some shared folders on another computer.

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It doesn't matter what's going on in terms of protocol and application in almost every situation.

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We have this session going on between two computers and a man in the middle attack is simply a third

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party that's sneaking in between these two conversations and doing whatever you will they're going to

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do.

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So when we're talking about a man in the middle attack there are two big parts to it.

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Number one you have to get in the middle.

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So that's going to depend on the technology and how that's going to work we're going to get into that.

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The second issue is as OK now that you're in the stream now that you're in the middle of that conversation

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what are you going to do about it.

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So to help us out what I would do is give you a kind of a set up and that's why I got all these computers

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here forked out.

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If we take a look over here what I have are two virtual machines.

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So if we take a look here you'll see this machine right here is running Windows 8 it's on 182 168 1.1

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90.

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And then over here is a Windows 10 machine and it's on 182 168 1. 146.

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You'll notice that it's 192 168 went out one for a default gateway.

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So what I have is this little router right here.

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This little home router he has a DHC server passing out 192 168 runs and he's going to be acting as

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our gateway now in this particular episode.

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What I want to do is keep things a little bit simpler so we're going to just all be on one network.

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But the fun part is is over here.

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What I'm running on this laptop is a very famous Linux distribution called Cali.

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So Cali is kind of like your best friend when it comes to all kinds of fun security things.

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It's just a big pile of fun toys all in one big piece.

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So if you take a look right here right now I don't have anything excited running on it other than this.

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So you can see that it is also on our network it's one into $161 1 0 7 and I can talk to both the router

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and my two virtual machines on this box so let's go ahead and draw up what we have right there.

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So what we have here is we've got our two windows machines the Windows 8 machine is 1 and 2 1 6 8 1

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1 0 9.

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And then we have the Windows 10 machine which is 192 168 1.0 146.

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Also we've got a router in here too.

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So the router is going to be 182 168 1.1.

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He'll be passing out DHC p.

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We have our attack machine which is going to be this colleague Linux box and at least for right now

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he's won 92 168 1.1 0 7.

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They're all on the same network.

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OK.

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So our first job with man in the middle attacks is to get into the middle somehow.

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We have to be able to as the attacker see the stream as it's going back and forth between the two different

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systems.

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Now the first way to do this is a wireless network and wireless is fantastic because in a perfect unencrypted

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world 10:42 wireless is completely open for anybody to read anything that they want to.

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So I can just take a laptop like this plug in the right type of wireless network card I can set that

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wireless network card in promiscuous mode and I can just grab everybody's packets I can just start sniff

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it away as they say and capture all these packets and I can get all the information I am in essence

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in between the streams in a wireless network.

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Now 10:52 Wireless has some protections for example if you use WPA or WPA too.

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First of all if you're using encryption that will certainly stop that will make that a lot harder.

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But even with encryption there's ways to decrypt sometimes.

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So WPA and WPA to also have isolation.

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So each computer on that wireless SS ID can connect to the wireless access point but they can't see

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anybody else so that's very beneficial.

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WEP is still a bit of a problem with WPA and WPA too.

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You basically got end to end encryption.

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Unfortunately with WEP you don't so yet one more reason to stop using WEP.

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It doesn't just stop with ATo to 11 though.

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Bluetooth is also susceptible to man and middle attacks.

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Bluetooth does have encryption built into it but Bluetooth counts on short distances and short duration

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of connections to make it hard for man in the middle of attacks.

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The other problem child is NFC now with NFC communication.

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What you have is a device or a Apple Pay or whatever you might be using something you like on a smartphone

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and it has a chip inside of there and it also accounts for the fact that it has to be extremely close

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to the other side of the conversation in order to work.

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So we do have these issues in all types of wireless but unencrypted aero to 11 is certainly the biggest

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problem of all.

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Now if you're using wireless you're probably already got about half the battle taking care of all you

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need to do is get some kind of card that's going to listen for all the packets and start pulling it

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in.

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However if you're in a wired network.

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Things change dramatically.

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If you're going to do a wired van in the middle attack things get a lot trickier.

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In a wired network packets are sent between systems based on MAC addresses or IP addresses or some other

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piece of information.

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So if we're going to do man in the middle in Wired attacks well then we're going to have to start the

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magical world of spoofing.

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So when we talk about spoofing we're talking about making something in the attackers address look like

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one of the victim's addresses.

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So for example I could spoof MAC addresses I could in essence tell my switch that oh this computer over

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here is actually that MAC address send the data to that one.

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We could also do what we could call IP spoofing.

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In that case what we're doing is we're telling the one computer on the end or either computer that go

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ahead and send it to me and then I can send it on over to the next guy so we can use that.

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We can also do things like using DNS addressing to get people to go to the wrong way.

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So what I want to do is go ahead and play with this a little bit and to do this we're going to use a

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wonderful program called acap.

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This is an old program it's been around for a long time.

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It is a free program that is marketed as an end as a penetration testing tool but it's actually a lot

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of things all in one cap is going to allow me to do the spoofing by different functions called poisonings.

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And not only will it do that but will actually grab the data for me and it will look through the data

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to give me the type of information I want.

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So we're going to keep it a little bit simple here.

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But let's go ahead and let me show you.

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Can at work one of the reasons that I like Carly Linnik so much is that it comes with so many handy

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tools and one of those tools is cap.

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So let's go ahead and get that guy started up and you can see how he does such a nice job about putting

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everything in a nice easy way for me to find stuff.

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So here under sniffing and spoofing EDR cap is one of many many handy programs that go ahead and get

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him started up.

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So let's go ahead and take a minute right now and take a look at our wired setup one more time what

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we're going to be doing here is we're going to be doing man in the middle attacks between our router

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and one of the Windows systems.

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So what I need do is get EDR cap set up in such a way that it can do that.

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Our cap is designed for man in the middle so it'll do stuff like say give me who I'm attacking.

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On one side give me who the target is on the other and then tell me what you want to do and we'll see

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that in the interface.

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So I'm going to begin what's called Unified sniffing and what it's doing at this point is just going

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out onto the wired network and seeing what hosts are out there.

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So that usually works pretty quickly.

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So what I'm going to do now is I'm going to tell him OK now chew sniffed find all the hosts on this

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network and if we're lucky we should be able to find all of our hosts.

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Let's see what happens.

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All right so it found three hosts.

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So let's take a look on the host list here.

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And there they are.

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So now keep in mind the attacking machine does not show up on here.

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So here's my router.

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And here are my two windows systems.

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So it does a really good job of sniffing just within the tool itself.

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So what we're going to do now is we have to pick targets so in this case I'm going to say target one

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is going to be the router and I'm going to pick the Windows 8 machine.

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Nothing special about that.

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And I'm going to make that target to.

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So we got the program ready to do some man in the middle attacking the first thing I'm going to ask

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this guy to do is what we call Mac spoofing.

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In this case what we're going to do is we're going to lie to the switch and basically tell the switch

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that we are the guy in between each one of these connections.

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So let's go and get him started.

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So I'm going to tell him to go ahead and get started.

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I could propagate this to other switches but in this case I only have one switch that's built in to

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the SOHO router.

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So I'm just going to hit OK now.

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I've went ahead and started the Mac spoofing.

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So right now this system is sending out all kinds of traffic out onto my network and going through Mac

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spoofing port stealing the exact same word.

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The problem here is that what do you do with this data.

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So basically anything that's going between this router and one of my Windows systems is being sent over

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to this guy right here so what do you do with it.

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Well that is the big issue a man in the middle attacks the number one function of man in the middle

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attacks more than anything else is to garner data is to do data exfiltration as they say.

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We want to grab some of that data usernames passwords images whatever we might want to grab.

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So what's going to do the grabbing.

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Well that could be a bit of an issue.

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So one of the things we could use is for example wireshark so good old Wireshark.

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Now one of the things you're going to see right here is you see all of these arms and this is all this

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noise that's being generated by the attacking system and it's creating all of these what are called

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gratuitous ARP addresses and it's going to go ahead and confuse the geezers out of the system.

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So the thing you do have to watch out for is all of this noise that's going out.

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Any good intrusion detection system would catch this and be very very nervous.

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Now the other nice thing about tools like EDR cap is that EDR caps relieve you from the need of having

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to use things like wireshark because EDR cap is a man in the middle tool.

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Not only will it go ahead and do the naughtiness for us but the other thing it will do is begin looking

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at that data and grabbing stuff.

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So what I want to do is I'm going to turn off the port stealing and we're going to move it up to IP

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spoofing.

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And in this case what we're going to be doing is an art poison.

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Now keep in mind every IP system on a network has a cache of IP addresses to mac addresses.

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This is called There are cash.

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So when we're are poisoning what we're doing is we're going to tell our cap to start lying to the other

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systems and not saying anything to the switch.

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It lies to the other systems.

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So the other systems will think that a particular IP address or going to has this MAC address.

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What they'll end up doing is that particular IP address is going to be to the attackers address.

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So let's go ahead and set up our poisoning.

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OK so to set up our poisoning I've got my two targets and what I'm going to do now is I'm going to start

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a man in the middle attack.

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And I just go to our poison right here.

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And I want to sniff both of the remote connections and I could also poison one way in this case.

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We want to be able to grab both sides of the conversation.

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So I'm just going to hit.

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OK.

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This time with an R poised Let's go ahead and actually grab some traffic.

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So what I'm going to do is this little router has a web interface like most of these routers do.

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And I'm going to go to one of these windows machines and just access this router.

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So let's go ahead and do that.

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Not on the Internet so it's not going to be happy.

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And I know my router's address is one I do once actually 1.1.

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So I actually hit the router right here.

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Now what I need to do is log in to do anything.

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Anybody can see this page but if I want to make any changes it's going to force me to log in.

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So I'm going to type in Bips you type in the username and the password and I log in.

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Now let's go over here.

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Let's take a look at our cap.

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Look what's happened here.

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The moment I did this so let me get the right spot.

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So you can see the username and my password is being captured by Edgar cap.

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This is a great example what makes EDR cat particularly convenient.

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So not only does it do the poisoning for me but it also does the sniffing for me and it's also smart

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enough to know to look for usernames and passwords for common protocols like HTP or Telenet or something

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like that.

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So our cap is very convenient because it does everything in one package but don't think that all packages

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work this way.

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It's just convenient that it does the attacking and it does a sniffing and then it goes through the

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data and finds the stuff that we're looking for.

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Normally this would be done with separate packages.

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That's why I like enter cap.

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So there's just one example of using art poison you again are poisoning is very noisy.

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It's actually sending out packets to the different targets lying to them so that there are caches are

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confused.

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But that works out pretty well and it does make a big pile a mess out there unfortunately.

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So what I'm going to do here is I'm going to do is a D.H. piece spoofing.

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So I'm going to start up DHP and in essence he's going to pretend to be a DHP server and I don't want

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to mess with anybody's IP addresses.

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But what I am going to do instead is I'm going to mess with the DNS information I have to type in the

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net mass because that's just how the program wants me to do it.

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Now here I can type in any DNS server IP address so it's not going to take the default DHP it's going

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to take whatever I put right here so I'll make something up.

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So I can put anything in here.

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I'm going to hit OK.

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And now it's going to start.

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DHC spoofing but only changing the DNS information.

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So what I've done now is every system on my network that uses DHC IP.

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I'm not messing with its default gateway I'm not Missee with its IP address I'm not Miskin with messing

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with it subnet mask on doing as I'm telling them all.

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A new DNS server that they didn't have before.

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So we could do a lot of cool DNS stuff with this.

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Let me give you one quick example.

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Once we'd gone ahead and poison the DNS using the DHC tool we can in essence spoof DNS servers.

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So for example one of the cool things I could do here is the next time somebody opens up their web browser

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and they want to go to w w w dot whateva dot com.

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If that system doesn't know the IP address for that web server it's going to go out and send a DNS request.

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Now what we could do is we could have a rogue DNS server on that particular IP address.

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So all the systems will go to that server and that particular server can point them to someplace evil.

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So we could have them type in WWII Google dot com.

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And because their DNS servers are evil server we could send them to someplace naughty and that's just

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one example of evil things you can do with DNS poisoning.

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Now the exam covers a few other things that are kind of man in the middle a type of attacks.

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But in my opinion they're not.

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But we're just going to go ahead mention them here.

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Anyway one of the things that we run into is what we call you are highjacking better known as typo squatting.

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Now what we're talking about here is if somebody has a Web site like Google and then somebody goes ahead

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and gets the domain g o g g e l get the idea.

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So because someone does a typo they will in essence be directed to someone else's site.

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It's not really injecting yourself in the middle of a conversation it's just deflecting somebody to

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another place.

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But it is considered man in the middle so we're going to go ahead and bring that up as well.

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So the other issue you can run into is called Domain highjacking domain highjacking is simply somebody

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doesn't keep a domain updated.

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I've done this myself.

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I have so many you are Elle's that I keep around.

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And there was a domain I had for a long time and I just forgot to read up the domain the domain ran

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out and somebody grabbed it really really quick and put a whole bunch of offensive material on there

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and they said well we'll sell it back to you for a lot of money and I had to pay because it was really

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really offensive.

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Now everything we've talked about so far is simply ways to get to a stream.

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As a man in the middle attack we've had some reference to some of the things we can do.

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And one of the things we do is we scrape data and we try to get information.

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And we saw that with EDR cap but there's some other stuff you can do so let's just take a moment to

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talk about what can we do once we're in the stream.

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So you would think the most perfect thing you could always do with man in the middle attacks is simply

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grab the data and look at it.

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Well that is good.

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And that's something we'd like to do a lot.

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But the other thing you can do is do something what's called a replay attack.

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This tends to be more convenient for secure communications.

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So for example I've got some type of secure communication protocol between two systems.

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I'm not interested in reading their data.

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What I'm interested in is getting the username and password now I'm not going to able to get their password.

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But the client in one particular example could be sending out a username and a hash.

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And if I get the username and a hash I have all the information so that later I can replay that over

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to the server and log in as that person anytime I want.

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That's the big danger to replay attacks once you get that information you can keep logging in as many

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times as you want to do whatever you need to do replay attacks even get into the world of certificates

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as well.

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You can do a lot of interesting things with that but I'm going to save all of that type of information

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for other episodes that specify exactly web pages.

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So hang on to that one.

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The other thing we can do is what's known as a downgrade attack.

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This is particularly useful for things like web pages.

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We've had a lot of different types of protocols starting with good old SSL and different versions of

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T.L. s and each one is better than the next.

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But if I can make a client talk to a web server and go look I want a secure web page but I can only

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do SSL.

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That makes it a lot weaker than the more advanced VLSI version.

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So if we have a web server that allows that to happen we can take advantage of that via what's known

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as a downgrade attack.

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Now the last thing I want to talk about is called session highjacking session highjacking basically

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means two people are already talking.

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They're already up and running.

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They're communicating what I'm going to do is get in the middle of that communication and I'm going

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to inject information in there and I'm going to be able to do naughty things now.

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Session hijacking is a incredibly difficult tool to use because what you have to do is take advantage

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of a real time connection that's taking place right now.

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However there is a great simplified version of that and it's been around for years and years and it's

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called Fire sheep.

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So here's a picture of fire sheep right here.

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All fire sheep does is it uses on unencrypted wireless connections.

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It performs a session hijack and literally connects into whatever is taking place.

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So here's a Facebook page that's being loaded.

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And since I've already logged in I've just caught in the middle of the session I've gone ahead and hijacked

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it.

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I could even make changes to it.

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So when it comes to a man in the middle attack remember there's always going to be two parts to the

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equation.

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Number one what are you going to do to get into the stream.

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And then number two what are you going to do with that data once you've got it.

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There are two separate issues and they're handled quite differently

21:54.260 --> 21:58.030
in.
